16 days in Italy Itinerary
Created using Klarna Trips Italy trip planner
Start: Chicago
Fly
1
Florence
— 4 nights
Drive
2
Assisi
— 2 nights
Drive
3
Rome
— 3 nights
Train
4
Naples
— 2 nights
Ferry
5
Anacapri, Island of Capri
— 1 night
Ferry to Naples, Fly to Venice
6
Venice
— 3 nights
Fly
End: Chicago
Wed, May 1 - Thu, May 16
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View full calendar
Florence — 4 nights
©
Birthplace of the Italian Renaissance
Museum-lovers will appreciate Florence Academy of Fine Arts and Pitti Palace. Explore hidden gems such as Basilica San Miniato al Monte and Historic Centre of San Gimignano. Explore the numerous day-trip ideas around Florence: Pisa (Leaning Tower of Pisa & Duomo di Pisa). There's much more to do: examine the collection at Museo di San Marco, contemplate in the serene atmosphere at The Baptistery of St. John, admire the striking features of Basilica of Santa Maria Novella, and pause for some serene contemplation at Basilica of Santa Croce.
To find where to stay, other places to visit, ratings, and tourist information, read Florence online travel route planner.
Chicago, USA to Florence is an approximately 14-hour flight. The time zone difference moving from Central Standard Time (CST) to Central European Standard Time (CET) is 7 hours. Expect a daytime high around 71°F in May, and nighttime lows around 52°F. Finish up your sightseeing early on the 5th (Sun) so you can go by car to Assisi.
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To find where to stay, other places to visit, ratings, and tourist information, read Florence online travel route planner.
Chicago, USA to Florence is an approximately 14-hour flight. The time zone difference moving from Central Standard Time (CST) to Central European Standard Time (CET) is 7 hours. Expect a daytime high around 71°F in May, and nighttime lows around 52°F. Finish up your sightseeing early on the 5th (Sun) so you can go by car to Assisi.
Side Trips
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Assisi — 2 nights
©
City of Peace
Start off your visit on the 6th (Mon): contemplate in the serene atmosphere at Basilica di Santa Chiara, pause for some serene contemplation at Basilica Papale e Sacro Convento di San Francesco d'Assisi, then see the interesting displays at Museo della Porziuncola, and finally contemplate in the serene atmosphere at Basilica di Santa Maria degli Angeli. On the next day, explore the world behind art at Studio Moretti Caselli, then step into the grandiose world of Rocca Paolina, then learn about winemaking at Tili Vini Societa Agricola, and finally contemplate in the serene atmosphere at Eremo delle Carceri.
For more things to do, where to stay, and more tourist information, refer to the Assisi trip itinerary planner.
Traveling by car from Florence to Assisi takes 2.5 hours. Alternatively, you can take a train. In May in Assisi, expect temperatures between 72°F during the day and 52°F at night. Finish your sightseeing early on the 7th (Tue) so you can drive to Rome.
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For more things to do, where to stay, and more tourist information, refer to the Assisi trip itinerary planner.
Traveling by car from Florence to Assisi takes 2.5 hours. Alternatively, you can take a train. In May in Assisi, expect temperatures between 72°F during the day and 52°F at night. Finish your sightseeing early on the 7th (Tue) so you can drive to Rome.
Side Trip
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Rome — 3 nights
©
Eternal City
You'll explore and learn at Vatican Museums and Galleria Borghese. Next up on the itinerary: explore the ancient world of Pantheon, steep yourself in history at St. Peter's Basilica, enjoy breathtaking views from Museo Nazionale di Castel Sant'Angelo, and make a trip to Spanish Steps.
To find other places to visit, more things to do, maps, and other tourist information, you can read our Rome trip planner.
Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Assisi in May, Rome is a bit warmer at night with lows of 58°F. Finish up your sightseeing early on the 10th (Fri) so you can catch the train to Naples.
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To find other places to visit, more things to do, maps, and other tourist information, you can read our Rome trip planner.
Traveling by car from Assisi to Rome takes 2.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Assisi in May, Rome is a bit warmer at night with lows of 58°F. Finish up your sightseeing early on the 10th (Fri) so you can catch the train to Naples.
Side Trip
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Naples — 2 nights
©
Start off your visit on the 11th (Sat): explore the world behind art at Museo Cappella Sansevero, then pause for some serene contemplation at Duomo di Napoli, then explore the world behind art at Museo e Real Bosco di Capodimonte, and finally see the interesting displays at Museo Archeologico Nazionale di Napoli. Keep things going the next day: steep yourself in history at Pompeii Archaeological Park, shop like a local with Sol’Art Ceramiche, and then make a trip to Piazza del Plebiscito.
For ratings, maps, where to stay, and tourist information, go to the Naples trip planner.
You can take a train from Rome to Naples in 2 hours. Other options are to drive; or fly. In May in Naples, expect temperatures between 74°F during the day and 58°F at night. Finish your sightseeing early on the 12th (Sun) so you can ride a ferry to Anacapri.
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For ratings, maps, where to stay, and tourist information, go to the Naples trip planner.
You can take a train from Rome to Naples in 2 hours. Other options are to drive; or fly. In May in Naples, expect temperatures between 74°F during the day and 58°F at night. Finish your sightseeing early on the 12th (Sun) so you can ride a ferry to Anacapri.
Side Trips
Find places to stay May 10 — 12:
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Anacapri, Island of Capri — 1 night
©
Kick off your visit on the 13th (Mon): trek along Fortini Coastal Walk, get engrossed in the history at Villa San Michele, then take in the awesome beauty at Monte Solaro, then explore the striking landscape at I Faraglioni, and finally admire the natural beauty at Giardini di Augusto.
To find more things to do, photos, where to stay, and more tourist information, use the Anacapri trip planner.
Traveling by ferry from Naples to Anacapri takes 1.5 hours. In May in Anacapri, expect temperatures between 74°F during the day and 60°F at night. Wrap up your sightseeing on the 13th (Mon) to allow time to travel to Venice.
more
To find more things to do, photos, where to stay, and more tourist information, use the Anacapri trip planner.
Traveling by ferry from Naples to Anacapri takes 1.5 hours. In May in Anacapri, expect temperatures between 74°F during the day and 60°F at night. Wrap up your sightseeing on the 13th (Mon) to allow time to travel to Venice.
Side Trip
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Venice — 3 nights
©
City of Romance
Museum-lovers will appreciate Doge's Palace and Peggy Guggenheim Collection. Step off the beaten path and head to San Giorgio Maggiore and Cannaregio. Next up on the itinerary: explore the activities along Canal Grande, enjoy breathtaking views from St Mark's Campanile, explore the world behind art at Gallerie dell'Accademia, and admire the striking features of Basilica di San Marco.
To see reviews, traveler tips, ratings, and other tourist information, refer to the Venice road trip planning website.
You can do a combination of ferry and flight from Anacapri to Venice in 4.5 hours. Alternatively, you can do a combination of ferry and train; or do a combination of ferry and car. Traveling from Anacapri in May, Venice is little chillier at night with lows of 55°F. Wrap up your sightseeing on the 16th (Thu) to allow time to fly back home.
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To see reviews, traveler tips, ratings, and other tourist information, refer to the Venice road trip planning website.
You can do a combination of ferry and flight from Anacapri to Venice in 4.5 hours. Alternatively, you can do a combination of ferry and train; or do a combination of ferry and car. Traveling from Anacapri in May, Venice is little chillier at night with lows of 55°F. Wrap up your sightseeing on the 16th (Thu) to allow time to fly back home.
Find places to stay May 13 — 16:
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Italy travel guide
Italy is a land of high fashion, fine art, exquisite architecture, luxury sports cars, outstanding cuisine--and an insatiable taste for "la dolce vita." It's also home to the greatest number of World Heritage Sites in the world, making it an ideal place for your next holiday. The country boasts a varied landscape of mountain ranges, alpine lakes, and coastal towns, so it's no wonder travelers often refer to it as the bel paese (beautiful country). With so many places to visit, visitors often have a difficult time planning their itinerary. The smaller villages each feature a distinct character and a blend of architecture, art, and cuisine. In the country, you'll find countless archeological sites dating back to Roman times and beyond. The country's cities and seaside resorts are cosmopolitan powerhouses with museums, galleries, restaurants, shops, open-air markets, and pedestrian-friendly historic areas.
